EDGEWISE PROTONATED CYCLOPROPANE IN GAS PHASE-COUPLING OF UNIMOLECULAR [1.1]-H2-ELIMINATION FROM C3H7+ AND RING-OPENING OF CYCLOPROPYL CATION

被引：36

作者：

SCHWARZ, H ^{[1
]}

FRANKE, W ^{[1
]}

CHANDRASEKHAR, J ^{[1
]}

SCHLEYER, PV ^{[1
]}

机构：

[1] UNIV ERLANGEN NURNBERG, INST ORGAN CHEM, D-8520 ERLANGEN, GERMANY

来源：

TETRAHEDRON | 1979年 / 35卷 / 16期

关键词：

D O I：

10.1016/0040-4020(79)85056-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on energetic data (activation energy), kinetic isotope effects and MINDO/3 calculations it is suggested that unimolecular loss of H2 from C3H7+ proceeds via a transition state (10) involving synchronous loss of a hydrogen molecule (symmetry allowed [1.1]-elimination) and ring opening of the cyclopropyl to the allyl cation. Alternative mechanisms are discussed. © 1979.

引用

页码：1969 / 1976

页数：8

共 77 条

[61] A METHOD FOR MINIMIZING A SUM OF SQUARES OF NON-LINEAR FUNCTIONS WITHOUT CALCULATING DERIVATIVES [J].

POWELL, MJD .

COMPUTER JOURNAL, 1965, 7 (04) :303-307

[62] MOLECULAR-ORBITAL THEORY OF ELECTRONIC-STRUCTURE OF ORGANIC COMPOUNDS .19. GEOMETRIES AND ENERGIES OF C3H5 + CATIONS - ENERGY RELATIONSHIPS AMONG ALLYL, VINYL, AND CYCLOPROPYL CATIONS [J].

RADOM, L ;

HARIHARA.PC ;

POPLE, JA ;

SCHLEYER, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (20) :6531-6544

[63]

ROSENSTOCK HM, 1977, ENERGETICS GASEOUS I

[64]

Schlunegger U. P., 1975, ANGEW CHEM, V87, P731

[65] DETECTION OF FRAGMENT GENESIS IN MASS-SPECTROMETER - DADI MASS-SPECTROMETRY AS AN AID IN STRUCTURE-ANALYSIS OF ORGANIC COMPOUNDS [J].

SCHLUNEGGER, UP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1975, 14 (10) :679-688

[66]

SCHOLLKOPF U, 1967, TETRAHEDRON LETT, P3639

[67]

SCHWARZ H, 1977, Z NATURFORSCH B, V34, P488

[68]

SIEHE ZG, 1973, ACCOUNTS CHEM RES, V6, P53

[69]

Thomas AF, 1971, DEUTERIUM LABELLING, P317

[70]

THORNTON EK, 1973, ISOTOPE EFFECTS CHEM

← 1 2 3 4 5 6 7 8 →